Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea is Maui's most refined resort area, offering a curated selection of luxury vacation rentals. Choose from spacious oceanview condos, private beachfront villas, or gated residences-each within walking distance to top beaches like Wailea Beach, Polo Beach, and Ulua Beach. With championship golf, fine dining, luxury spas, and The Shops at Wailea nearby, Wailea is perfect for honeymoons, family vacations, and long-term stays.
Browse Wailea Vacation Rentals by condo/hotel name:
Wailea vacation rentals combine the comfort of home with the indulgence of resort amenities. Whether you prefer a villa with sunset views, a quiet garden retreat, or a beachside condo steps from the surf, Wailea's neighborhoods cater to every kind of traveler.
Top Wailea Vacation Rental Communities
Oceanfront and Beach Access Villas
- Wailea Beach Villas – oceanfront penthouses and beachfront villas
- Polo Beach Club – beachfront condos with panoramic views
- Wailea Point Village – gated luxury with prime oceanfront location
- Mana Kai Maui – beachfront condos on Keawakapu Beach
- Wailea Elua Village – beachfront property with pavilion and pools
Resort-Style Villas & Upscale Condos
- Ho'olei at Grand Wailea – spacious 3-bedroom villas with cascading pool
- Wailea Ekahi Village – low-rise condos with ocean views and tropical gardens
- Wailea Ekolu Village – hillside condos near golf and beaches
- Wailea Grand Champions Villas – golf course condos with pools
- The Palms at Wailea – Mediterranean-style condos with large lanais
Why Stay in Wailea?
- Access to Wailea Beach, Polo Beach, and Keawakapu Beach
- Home to Wailea Golf Club and scenic coastal trails
- Upscale dining and retail at The Shops at Wailea
- Quiet, landscaped communities perfect for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-tranquil surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic retreat or a long-term tropical escape, Wailea vacation rentals provide the perfect home base for a luxurious island experience.
Wailea Ekahi Village 50C - 1 Bedroom Garden View Condo
Experience the ultimate in island luxury with a stay at Wailea Ekahi 50C, a beautiful one-bedroom, one-bathroom vacation rental situated in the heart of Wailea. This elegant ground floor condo offers the perfect blend of modern comfort and tropical charm. From the...
Wailea Ekahi Village 49C - 1 Bedroom Ocean View Condo
Wailea Ekahi Village 49C is a charming vacation rental located in one of the most popular Wailea vacation rental communities. This one-bedroom ocean-view condo offers a perfect blend of comfort, luxury, and tropical ambiance, making it an ideal destination for travelers...
Wailea Ekahi Village 49B - 1 Bedroom Ocean View Condo
Wailea Ekahi 49B is a stunning ocean view condominium located in the heart of the renowned Wailea resort area. Nestled along the pristine white sand beaches of Keawakapu Beach, this luxurious condo complex offers sits on 34 acres of lush tropical landscaping. Spanning...
Wailea Ekahi Village 47E - 1 Bedroom Garden View Condo
Wailea Ekahi 47E is a beautiful vacation rental nestled within the landscaped 32 acres of lush tropical gardens that make up Wailea Ekahi Village. This condo offers a precise blend of comfort and tropical elegance, making it the perfect home to relax and unwind after a...
Wailea Ekahi Village 47D - 1 Bedroom Ocean View Condo
Wailea Ekahi 47D is a spacious and beautifully updated one-bedroom, two-bath condo located in one of Wailea’s most sought-after beachfront communities. Perched on a gentle slope, this upper-level unit offers breathtaking ocean views from the private lanai, perfect for...
Wailea Ekahi Village 47B - 1 Bedroom Garden View Condo
Welcome to your tropical retreat at Wailea Ekahi Village 47B—an ideal vacation escape for families or a group of friends. This beautifully appointed ground-floor residence offers the perfect blend of comfort, space, and convenience. With serene garden views and easy...
Wailea Ekahi Village 26D - 1 Bedroom Garden View Condo
Escape to paradise in this beautifully appointed one-bedroom vacation rental nestled in the lush tropical gardens of Wailea Ekahi Village. Located on Maui’s sunny south shore, 26D is a tranquil second-floor unit that offers the perfect blend of privacy, comfort, and...
Chic Coastal Living in the Heart of Wailea
A brand-new split air-conditioning system has been installed throughout the property, ensuring year-round comfort with contemporary efficiency and quiet operation.This is a NEW listing and it's gorgeous! We are confident you will have a great experience. Welcome to...
NEW KBM Resorts | FREE CAR | Grand Champions | Remodeled 1-Bedroom Villa in the Heart of Wailea! GCH-181
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Wailea Ekolu 1608 | 1 Bedroom | Prime Wailea Location with Golf Course Views
Experience the beauty and convenience of Wailea from this tastefully appointed 1-bedroom, 2-bath condo at Wailea Ekolu 1608. Perfectly situated along the fairway of Wailea’s prestigious Blue Golf Course, this ground-level home offers comfort, privacy, and stunning...
Wailea Ekolu 804 | 1BD/2BA | Ocean Views | Prime Wailea Location
Interior photos coming soon. Wailea Ekolu 804 | 1BD/2BA | Ocean Views | Prime Wailea LocationWelcome to Wailea Ekolu 804, a beautifully appointed one-bedroom, two-bathroom retreat perfectly positioned in the heart of Wailea. This spacious condo is nestled along the...
NEW! KBM Resorts | Ocean Views | FREE CAR | Wailea Ekahi | 1-Bedroom Condo with Luxury Amenities! WKV-45C
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Refined Resort Wailea Oceanview Vistas
Summary:Perched overlooking Wailea on southern Maui, this wonderful two-bedroom condo is a dreamy escape into open airy luxury. With incredible ocean views, and every amenity a Maui visitor could hope for, guests will fall in love with Wailea's beautiful lushness, while...
WAILEA POINT Sweet 2 Bedroom/3 Bath Oceanview Condominium
Please call or email us about the dates for your visit. Free Car promotion! Want a mini-Cooper or similar ride while you're here on Maui - Ask us! New media posted! Check out the new photos and video. Make yourself home at Wailea Point Village 3003. A first-floor...
Tranquil Stay at Wailea Ekahi Oceanfront Complex-2 Beds-Balcony
Relax in our 1BR/1BA condo at Wailea Ekahi Village, perfect for up to 4 guests. This renovated upstairs unit features a California King bed, Queen Murphy bed, a fully stocked kitchen, and modern amenities like WiFi, AC, and a bidet-equipped bathroom. Enjoy a private...
Cozy 1-bedroom condo with AC, WiFi in lovely Wailea-Makena
This enchanting condo in Wailea-Makena is the perfect home base for your trip. With 1 bedroom featuring a cozy king bed and a stylish living room with a sofa bed, this awesome property is ideal for couples or small families. Open floor plan living area which opens to a...
Wailea Ekahi 6E-Gorgeous Condo, #1 Location, Serene/Private, steps to Pool/Beach
***Please note: This unit is under NEW ownership. The previous owner had a 10/10 rating with 67 reviews!LOCATION, LOCATION, LOCATION is everything at Ekahi Village! Ekahi Village is a premiere condo complex in beautiful Wailea, Maui. Unit 6E is perfectly situated within...
Oceanview Paradise: Tropical Retreat in Wailea
Welcome to our beautiful, elegantly remodeled 2-bedroom, 2-bathroom condo in the prestigious Wailea Grand Champions Villas. Perched on the 2nd floor, this luxurious condo offers breathtaking ocean views and a spacious, open floor plan with tasteful modern finishes.Upon...
Impressive Wailea Point 2 Bedroom+Loft/2 Bath Oceanview Condominium
Yes, you can rent a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment. Each of our privately...
Wailea Point 3 Bedroom/3+ Bath Oceanview Condominium #2503
Yes, you can enjoy a holiday and vacation stay at Wailea Point, the iconic red roofs on Maui's wonderful southern shore; and at a rate lower than a suite at the Wailea hotels. 2503 just may be the 'best location in the whole property'; with an expansive outdoor lanai...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
Palms at Wailea Villa 1210 Garden Deluxe 1 BD 2 BA
This charming one-bedroom garden-view villa is located in Maui’s sought-after Wailea resort community. With a full kitchen, open concept living area, and private patio, it’s a perfect base for enjoying nearby beaches, world-class golf, and island dining. Villa 1210...
Large Charming Ocean View studio in terrific Wailea with WiFi, AC
Comfort meets convenience. Our spacious bedroom suite features two queen beds, a covered lanai overlooking gorgeous tropical scenery and stunning ocean sunsets. Nearby tennis/pickleball courts, and golf, active leisure is just steps away. AC wall unit and ceiling fan...
Luxurious Wailea Ekahi 19A - Ground Floor with Ocean Views & Easy Beach Access
Wailea Ekahi #19A – Spacious Townhouse Comfort Near Keawakapu BeachWelcome to Wailea Ekahi #19A, a rare and spacious 2-bedroom, 2-bathroom townhouse nestled within the beautifully landscaped Wailea Ekahi Village. Located just steps from world-famous Keawakapu Beach and...
Palms at Wailea Villa 2203 Garden Deluxe 1 BD 2 BA
Tucked within the world-famous Wailea resort community, this garden-view villa offers a serene retreat surrounded by tropical beauty. Enjoy a spacious layout, full kitchen, and breezy patio—all just a short stroll from beaches, restaurants, and luxury shopping. Villa...
Palms at Wailea Villa 1103 Ocean View 1 BD 2 BA
- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 473 square feet deck- Bedroom with 1 king- Queen sofa bed in living area- 1022 square feet / 95 square meters-...
Palms at Wailea Villa 805 Garden View 2 BD 2 BA
- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 219 square feet deck- Master bedroom with 1 king bed- 2nd bedroom with 1 queen bed- Queen sofa bed in living area-...
Palms at Wailea Villa 301 Garden Deluxe 1 BD 2 BA
Relax in this one-bedroom villa with tranquil garden views in the heart of Wailea’s resort community. Designed for comfort and convenience, it features a full kitchen, airy living space, and easy access to beaches, golf courses, and walking paths. Villa 301 Garden 1...
Palms at Wailea Villa 1805 Garden View 2 BD 2 BA
- Ground floor unit- Kitchen includes dishwasher, stove top/oven, microwave, refrigerator, coffeemaker, blender, cookware and tableware- 473 square foot lanai- Master Bedroom with 1 king size bed and guest bedroom with a Queen size bed- Queen sofa bed in sunken living...
Palms at Wailea Garden Villas 1 Bedroom 2 Bath
A peaceful one-bedroom villa with lush garden views, located in Maui’s renowned Wailea Resort community. Perfect for a relaxing getaway, it features a full kitchen, open living space, and private lanai – just minutes from pristine beaches and championship golf.Garden...
Palms at Wailea Garden Villas 2 Bedroom 2 Bath
Relax in a spacious two-bedroom villa with peaceful garden views, located in the prestigious Wailea resort community. Featuring a full kitchen, open living area, and private patio, it’s perfect for families or small groups seeking a serene Maui getaway. Garden View 2...
Palms at Wailea Garden Deluxe Villas 1 BD 2 BA
Experience elevated island comfort in a deluxe one-bedroom villa with lush garden views, located in Maui’s exclusive Wailea resort community. Enjoy a spacious layout, full kitchen, and private patio—just minutes from beaches, golf, and fine dining. Garden Villa Deluxe 1...
Palms at Wailea Ocean View Villas 2 Bedroom 2 Bath
Take in breathtaking ocean views from a spacious two-bedroom villa in Wailea’s resort community. Featuring a full kitchen, open living area, and private patio, it’s the perfect retreat for families or friends seeking a relaxing Maui escape. Ocean View Villa 2 Bedroom 2...
Palms at Wailea Ocean View Villas 1 Bedroom 2 Bath
Enjoy stunning ocean views from villas featuring a full kitchen, spacious living area, and a private patio; it’s the perfect spot to relax while soaking in Maui’s breathtaking coastal beauty. Ocean View Villa 1 Bedroom 2 Bath• Kitchen includes microwave, stovetop/oven,...
Palms at Wailea Garden Deluxe Villas 2 BD 2 BA
Deluxe garden-view villas offer a tranquil retreat surrounded by lush tropical landscaping in Wailea’s resort community. With a full kitchen, inviting living space, and private patio, it’s an ideal home base just minutes from beaches and golf courses. Garden Villa...
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802
Wailea Elua #1802 – Luxurious Oceanfront Retreat with Panoramic ViewsExperience upscale coastal living at Wailea Elua #1802, a beautifully renovated second-floor, 1-bedroom, 2-bathroom oceanfront condo located in one of Wailea’s most desirable beachfront communities....
New Listing | Maui Oasis at The Grand Champions unit 53
Forget your worries in the spacious and serene space. This recently refreshed bright, 1 bedroom, 2 bath condo is perfect for up to 4 guests to enjoy all of Maui's luxury establishments within walking distance. Retreat to the ground floor lanai where you will soak in an...